While Porter has been winning the red carpet at award shows for years now, there is one particular look that caught everyone's attention. In 2019, the actor showed up at the 2019 Oscars red carpet in a tuxedo dress designed by Christian Siriano, per Harper's Bazaar. This took the standard garment men are supposed to wear to award shows and flipped it on its head. He was able to showcase both a feminine and masculine look for the world to see.

Porter told Vogue about the process of creating the tuxedo dress. "We wanted to play between the masculine and the feminine. This look was interesting because it's not drag. I'm not a drag queen, I'm a man in a dress. He came up with a tux on the top, and a ballgown that bursts out at the bottom."

Porter was determined to shift the idea of what men can wear on the red carpet that night. Ultimately, he wants to change the world's definition of gendered clothing. He told Variety, "I think that we as artists ... have the power to change the molecular structure of people's hearts and minds and change the world. That dress changed the world."